Water → HCID 19430415, compound

HRID 863446Notes

Reaction equation

HRID 863446 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([C:13]2[N:14]=[C:15]3[C:20]([CH2:21][OH:22])=[CH:19][CH:18]=[CH:17][N:16]3[CH:23]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.O>C(Cl)Cl.CS(C)=O>[CH:21]([C:20]1[C:15]2[N:16]([CH:23]=[C:13]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:14]=2)[CH:17]=[CH:18][CH:19]=1)=[O:22]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19696491HCID 19696491, compound

Product 1

HCID 19430415HCID 19430415, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 14.8 ml of dimethyl sulphoxide and 45 ml of methylene chloride is added dropwise to 8.7 ml (110 mmol) of oxalyl chloride in 220 ml of methylene chloride at -60° C. under inert conditions. 19.5 g (87 mmol) of 2-phenyl-8-hydroxymethyl-imidazo[1,2-a]pyridine in 90 ml of methylene chloride and 45ml of dimethyl sulphoxide are then added dropwise at -60° C., while stirring, and the mixture is stirred at -60° C. for 15 minutes end at -10° C. for 1 hour. 60.9 ml of triethylamine are now added and the mixture is stirred at -10° C. for 5 minutes and then allowed to come to room temperature. For working up, water is added, the organic phase is separated off and the aqueous phase is extracted twice more with methylene chloride. The combined organic phases are washed with saturated NaCl solution, dried over Na2SO4 and concentrated on a rotary evaporator. Stirring of the residue with ether gives 16.4 g of crystals (=73.8% of theory), which are chromatographed over silica gel for removal of chlorinated by-products.

Workup

  1. stirringthe mixture is stirred at -60° C. for 15 minutes end at -10° C. for 1 hour
  2. stirringthe mixture is stirred at -10° C. for 5 minutes
  3. customto come to room temperature
  4. customthe organic phase is separated off
  5. extractionthe aqueous phase is extracted twice more with methylene chloride
  6. washThe combined organic phases are washed with saturated NaCl solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated on a rotary evaporator
  9. stirringStirring of the residue with ether

Sources & evidence

ORD record
ord-bf8f9da80ffc4aa58fb8296f40fc23c0
Source dataset
uspto-grants-1998_02
Patent number
US05721248

Reaction notes

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